Cited by Cobalt-Catalyzed Highly α-Stereoselective Glycosylation of Glycals

Streamlined Access to Peptidoglycan Biosynthesis Terminator GlcNAc-1,6-anhydro-MurNAc DOI

Yue Zhang,

Xiao-Lin Zhang,

Han Ding

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: 27(2), P. 698 - 703

Published: Jan. 6, 2025

GlcNAc-1,6-anhydro-MurNAc is a key peptidoglycan elongation terminator of biological and medicinal importance. Herein, we present concise approach to this molecule in 12 steps with an overall 25% yield using d-glucosamine as the sole starting material. Our synthesis features formation 1,6-anhydro-MurNAc building block by intramolecular glycosylation selective conversion phthalimido group MurNPhth moiety, paving way for antibiotics new killing mechanism targeting bacterial transglycosylase.

Language: Английский

Citations

Strain-Release Glycosylation of Thio- and Selenoglycosides Enabled by Activation of Donor–Acceptor Oxiranes with Catalytic TfOH DOI

Xin-Yu Fang,

Liu Xingle,

Jiaying Shen

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: April 22, 2025

We have developed a strain-release glycosylation method for thio/selenoglycosides utilizing donor-acceptor oxiranes (DAOs) and triflic acid (2 mol %) via C-C bond cleavage under ambient conditions. This protocol is effective acid-sensitive sterically hindered substrates, demonstrating broad applicability. Experimental results DFT calculations reveal that DAO/TfOH-derived zwitterionic oxocarbenium species activate donors glycosyl zwitterion intermediates, facilitating glycosidic formation proton transfer. approach pioneers epoxide-mediated activation, offering mild, efficient platform diverse glycoside synthesis advancing methodologies in carbohydrate chemistry.

Language: Английский

Citations

Copper-Catalyzed Asymmetric Nucleophilic Opening of 1,1,2,2-Tetrasubstituted Donor–Acceptor Cyclopropanes for the Synthesis of α-Tertiary Amines DOI

Shouang Lan,

Qinqin Cui,

Defu Luo

et al.

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 26, 2024

Catalytic asymmetric transformation of donor–acceptor cyclopropanes (DACs) has been proven to be a highly valuable and robust strategy construct diverse types enantioenriched molecules. However, the use 1,1,2,2-tetrasubstituted DACs form products bearing quaternary stereocenters remains long-term unsolved challenge. Here, we report copper-catalyzed aminative ring opening tetrasubstituted alkynyl that delivers myriad α-tertiary amines with high levels enantioselectivities. The alkyne, amine, ester moieties within enable further applications, including synthesis bioactive Mechanistic studies indicate zwitterionic intermediate copper-acetylide unit plays key role in process, which represents new mode for achieving catalytic DACs.

Language: Английский

Citations

Cobalt-Catalyzed Highly α-Stereoselective Glycosylation of Glycals DOI

Liu Xingle,

Qiu-Qi Mu,

Li Xu

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 22, 2024

Following the satisfactory catalytic performance of cobalt in

Language: Английский

Citations